


Creepypasta Dating Scenarios

by ThisShipHasSailed



Category: Creepypasta - Fandom
Genre: Creepypasta, Eventual Smut, F/M, Gen, Love, Romance, Scenario, Scenarios, Sexuality, Smut, Violence, boyfriend scenarios
Language: English
Status: In-Progress
Published: 2019-06-10
Updated: 2019-06-10
Packaged: 2020-04-24 06:19:21
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,768
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19167535
Author URL: https://archiveofourown.org/users/ThisShipHasSailed/pseuds/ThisShipHasSailed
Summary: Creepypasta boyfriend scenarios, but with a twist!Includes: Jeff the Killer, BEN Drowned, Slenderman, Masky, Hoodie and Eyeless Jack. More may be added later if enough requests come in! You may request scenarios as well.Future chapters will include NSFW topics, such as sexuality, violence, etc.I will be updating every Monday unless otherwise specified.





	Creepypasta Dating Scenarios

Ben Drowned

_Rating: PG_

You had moved to the small town of Bristol only a week ago. The town had 5,375 people, with a church, a bar and grill, the “school zone”, a grocery store and an old park with one rusty slide, three swings and a sandbox that the local cats used as a litterbox. There were four sets of neighborhoods, too.

You lived in Green Valley, where the middle class dwelled. Your family had enough money to be comfortable, but not quite enough money to just spend recklessly. The house you and your family had moved into was a two-level abode, two bedrooms upstairs, one downstairs. Your parents took the master bedroom in the basement while you and your sister took the two upstairs bedrooms.

Your bedroom was the second largest. Your sister sat on your bed, looking around the room. She seemed jealous that she had gotten the smaller room while you had the larger one.

“Why do you get this bedroom? It’s not even fair. I had the smallest bedroom _last_ time!” She pouted, and you merely shook your head. Your sister was only ten, with you being eight years older.

“It’s because I’m older.”

“It’s not fair!”

“Life isn’t fair, Miranda.” You shot back, raising your brows at her. She merely huffed, crossed her arms over her chest with a look of irritation on her face. Your sister was strong in spirit, and didn’t like taking no for an answer. You two would probably fight over who got the room for the next few weeks.

“That’s what _mom_ says.” Miranda glared at you before literally slamming herself into the bed. You just shake your head and continue to decorate your new room.

Your bed was against the farthest wall running horizontally, with a spacious arching ceiling and a hanging light fixture in the middle. You had moved your dresser upstairs with your dad earlier that afternoon, and now it sat on the left side of the room. You still had to move your desk up, but that would be for tomorrow.

You’re going through a box before something twinkles at you from beneath a bunch of clothes. It’s a picture frame with you and all of your friends from back home. You feel your lip quiver as emotions run rampant through you, and you run your thumb over the glass. You’re going to miss them.

“Girls! There’s a garage sale going on next door! Why don’t you go outside and check it out?” Your mom called from down the stairs, and both you and your sister grumble.

“It’s hot outside!” Miranda groaned, and your mom merely tsked.

“It’s beautiful. You need the sun.”

You see this as an opportunity to get your sister out of your room, and you take it graciously. You set down the picture on the shelf before turning to Miranda, who had the biggest pouting face that you had ever seen.

“C’mon, let’s go. It’ll be fun.” You reason and she sighs out loud, now feeling as if going outside was a mildly better idea instead of sitting inside, complaining over who got what room.

So you and your sister walk downstairs, talk with your mom and then you’re outside in the summer warmth. It wasn’t all that hot, as the last few days had been nothing but rain and more rain. It felt humid, though, and you could feel it pressing against your skin like a tight-fitting shirt. You walk across the street, seeing the neighbor's garage sale set up.

Three tables stood on the driveway. Miranda’s eyes catch on a pile of stuffed animals and she was running over to it. You take your time, meeting your sister as she hugs a Pikachu plushie.

“Y/n! Can you buy me this? _Please?”_ You look down at your sister’s sweet, darling face, and with the power of a god, you respond with a smirk on your face.

“No.”

“What?! Why?!” She dragged, holding onto the plushie even tighter now.

“God, I’m kidding. I’ll get you it.” You reply before looking at the ear of the Pikachu, noticing the tag there. Five bucks, huh? Not bad.

You continue to browse, looking through the things that could possibly interest you. A fairy figurine caught your eye, and you picked it up to reveal an old, beaten up cartridge with _Majora_ scrawled in fat permanent marker. You were well versed in Legend of Zelda, though, and you instantly recognized it with mild interest.

There wasn’t a price tag on it. You looked up to see an old man, sitting in a lawn chair staring at you. You pause, feeling alarm shoot through you before you calmed yourself. He was just a harmless old man with a staring problem. He probably couldn’t even see you without his glasses, and you made your way over to him.

“How much for the game?” You asked, and he merely sniffed at you before glancing at the game.

“You can jus’ take it, girly. I don’ want it anymore.” He said, and you raised a brow. Hey, what can you say? You were glad to take the game off his hands. Your little sister came over then with the Pikachu in hand.

“I’ll take the Pikachu and the fairy, please.”

“Tha’ll be eleven bucks, girly.” You take out your wallet from your back pocket and pay up. You and your sister bid him farewell, and you leave back to your house with the Pikachu, the fairy and the game in hand.

 

Jeff The Killer

_Rating: PG-13 for Alcohol Use_

You and your best friend had been preparing this for a week now, and damn it you were excited. Not just excited, but ecstatic that you two would be attending a party and it wasn’t just any party. It was Tricia’s party, and she hosted the best parties north of the equator. At least, that’s what you thought.

You were all decked out. You wore a tight cocktail dress with flats. The outfit was from Goodwill, but you spruced it up and it looked to be an outfit from Gucci. Leah, your best friend, had done all your makeup. You had some experience in makeup, sure, but Leah would never let her best friend with just a bit of eyeliner and mascara.

“Oh, hell to the _no!”_ She had exclaimed before sitting you down in front of the mirror. Now, you two were at the party and having a great time. The music swelled with the bass, the piano and the guitars and the instruments. Then the voice started and you couldn’t help but swoon at the feeling of the rhythm flowing through your every move.

Leah was walking towards you with two red solo cups in her hands. She handed one of them to you before leaning forward to talk over the boom of the song.

“It’s vodka with some fruit! It’s supposed to be _super_ good.” Leah grinned at you, and you couldn’t help but grin right back. Leah was intoxicating, to say the least, and you took a sip of your drink to distract yourself. The alcohol burned your throat and made you cough, and Leah giggled.

“Stir it up a little, silly!” You felt yourself flush as you did so.

For the next few hours, you and your best friend partied your hearts out. You ended up seeing more of your friend group and moved to dance near them. They all greeted you with cheers and grins and laughter as you all drank, danced and partied in unison.

It was one of the most fun times in your life. That was probably the alcohol talking but you had gotten used to the burn, and it was no longer really something you noticed. The taste of the fruit mixed with the alcohol had you seeing stars, and you danced, danced, danced.

Leah was beside you again once a slow song started to a play. A few had already come on, but you had disappeared to the snack line to get a bag of chips, or another drink. This time, though, Leah meant business.

“Dance with me, baby.” Leah slurred, and you couldn’t help but laugh. She was adorable drunk, with her cheeks red and her gaze lidded as she stared up at you. You felt your heart skip a beat as you chugged the rest of your drink down, setting the cup on a table to be forgotten.

Leah’s hands landed on your hips, pulling you in close. You bit on your lip at the sight of her, and then she was sliding her hands to your back until she was hugging you, dancing slowly to the song.

You let out a content giggle as you rested your hands on her shoulders. Leah had always captivated you, and she kept looking at you with those _eyes_ and you couldn’t look away. Then, before you knew it, the song was over and Leah didn’t let go. She held you against her with that sweet, oh-so-drunk smile on her face.

“I love you, Y/n.” Leah announced, and you knew that you would need to get her home in one piece.

“I love you too, Leah. But we need to go home now.”

“No… the party is only… starting!” She protested, and you wiggled out of her hold. But it wasn’t long before your hand was in Leah’s, and you were leading her out to the driveway. You called an Uber, and waited with Leah on the sidewalk for a bit, ignoring a few of the couples making out by the house and in the bushes.

One strangler had come up to them, spoke a few choice words about being “absolutely shit-faced” and proceeding to throw up against a tree before passing out.

“He should be fine, right?” You murmured to Leah, who only giggled in response.

Someone out of the corner of your eye made you look towards the woods beside Tricia’s house. It was black in those woods, with a faint wind rustling the leaves. But something large and white was sticking out among the blackness, which made you raise your brows in confusion.

It was a person, and as you focused on the person you noticed dark red stains on the hoodie. Something was wrong, but you were too drunk to be able to make out what was actually wrong.

Then the Uber had arrived and that was your cue to leave. You ushered Leah into the car before getting in on the other side. As you shut the door, you looked back to see that the man was gone.

The next day you woke up with a raging headache. Leah was still out cold, sleeping on the other side of your queen sized bed. You groaned, getting out of bed to make a pot of coffee. It took you at least a half hour to make coffee, take a shower and pop four pills of pain-killer, and even then Leah remained asleep.

_Bzzt. Bzzt. Bzzt._

You could hear your phone vibrating on the dresser. You don’t remember putting it there. But then again you don’t remember a whole lot about what happened last night once you arrived in your dorm with Leah.

You unlocked your phone before scrolling through the texts.

_Have you heard from Jerry? I can’t find him._

_Did you hear? Jerry went missing._

_Yo, check out the news._

You furrowed your brows together before pulling up the news website on your phone, but once you did you felt your stomach drop.

_Jerry Figgins reported missing last night after a frat party gone wrong. Multiple stabbed, one dead, one missing. If you have any information on what happened, please contact the Renbold City Police._

You felt yourself beginning to remember the party. The songs, the dancing, the drinks. But you never remember anyone being stabbed, or killed, for that matter.

But you did remember that man in the woods with blood on the hoodie. You instantly felt apprehensive, frightened before you dialed the police station and you told them you saw a figure in the woods.

 

Slenderman

_Rating: PG-13 for drug use_

You were a dumb teenager in a forest with a bunch of your dumb teenage friends. It was the summer right before college would start, and you all agreed to camp out right before you all had to go your separate ways. You could feel your heart breaking, piece by piece, as the days went on.

You were going to miss these morons, no matter how dumb they were. You’ve grown up with a lot of them. Clarice popped up in Kindergarten, about a month after the school year had started. She had been out sick with the flu, and at that time most of the kids had already made their friend groups. So you had reached out your tiny, child hand and invited her to become a part of a two-person group: Clarice and Y/n.

Then, in third grade, Quinn and Jacob had joined. They had moved to your little town. Jacob’s parents had split while Quinn’s mom had passed away and her father could no longer take care of such a large house.

Jae showed up in seventh grade after you had begun your spooky, creepy supernatural phase. Jae had also been in that phase, and when your science teacher had paired you up with Jae you had made an unlikely friendship.

Last but not least was Rowan. Rowan was just Rowan, a nonbinary friend that you had met through a summer camp. Joe was as sweet as they came, and all of your friends loved Joe with all their hearts.

Rowan was also the person in the group that loved to push people to do better things with themselves. Sometimes, though, Joe didn’t have a great meter of what “good” and “bad” was. They always said that “There is no good or bad, it just is, man.” Then Joe would proceed to punch the arm of anyone closest and ask if it felt good or bad.

“So, as preplanned… I brought weed.” Rowan grinned devilishly. They took out a little baggie from their bag as well as a bowl. You couldn’t help but feel a bit cautious. You had never actually gotten high before, except for when you were put under to get a tooth taken out. But that didn’t count, right? But nonetheless, you were nervous about trying an illegal substance, yet so excited that you were _breaking the law!_ How scandalous.

Rowan did their thing with the bowl and weed before grabbing their lighter. They made eye contact with everyone there, making sure that everyone was comfortable as well as ready before explaining how to inhale, keep it in for a few seconds, then letting out the smoke.

“And for fuck’s sake, people, only take two or three puffs or you’ll get sick. Also-” They broke off, reaching right back into their bag to take out a few bottles of water.

“Trust me, guys, water will do wonders. Don’t be afraid to drink it. Now, if you don’t want to smoke that is fine. But just make sure to pass it on, okay? Okay.”

The next hour was just a fest of laughter, the scent of weed strong in the air. Every single one of you had taken a hit, with a few of you taking a two more. You, on the other hand… Well, just like how you were a dumb teenager… You were dumb.

You took six hits when nobody was watching. You don’t notice anything odd until about twenty minutes into the discussion and _hoo boy_ are you feeling the effects. You felt _good._ A little too good, but good nonetheless.

Everybody seemed so bright and funny, and you couldn’t stop giggling. Everything was funny and you could _not_ stop laughing. Soon enough it became apparent that your dumbass had smoked a little too much pot and Rowan was sitting next to you.

“You’re not supposed to smoke that much, Y/n.” They said softly while Clarice and Jacob talked about aliens beside you. It was all so surreal.

You leaned against your friend, closed your eyes for a moment with a wide grin spread across your face. You sat there for a good while until an annoying buzz began to play through your head. At first, you had just assumed it was the weed playing with you. But then it became persistent with a slight pain ringing through your ears. You moaned pitifully, looking over to Rowan for sympathy.

“My head hurts…” You mumbled, and Rowan chuckled, sliding their fingers through your hair.

“You’ll be okay, Y/n.” They replied, massaging your back as you leaned against them.

You opened your eyes, your gaze set on the woods all around you. It was thick, with leaves and branches and brush and you wondered how your little clown posse had managed to get all the way here. In the distance, though, you noticed an odd sound coming from the trees.

A buzzing sound that rolled through your head like a boulder, hot and heady with no resistance. It was like little shocks being administered to your brain, and it set you apart from yourself. It was like a mini seizure, but only effecting your head.

Then, you blinked for a second and there was something in the woods. You could feel the hairs on the back of your neck begin to stand up as gooseflesh broke out along your arms. You couldn’t stop staring at the _thing_ that stood in the trees. You wondered how you had even noticed it in the first place when you saw its face.

There was no face. It was just a blank slate, completely white and it made you want to run as fast and as far as you could away from that place.

“Rowan… I don’t want to be here.”

“Shh… It’s okay.”

You watched as the thing began to shake its head back and forth, twitching. It was tall, so tall that you could barely tell how tall it was as it touched one of the trees with a long, gaunt hand.

You blinked again, and it was gone. You blinked again, and your eyes remained closed until morning.

Eyeless Jack

_Rating: PG_

You had never slept soundly like your family and your friends. You tossed and turned and woke up at the faintest sound, like your cat sneaking across the floor, or the quietest wind brushing against your bedroom wall. Melatonin, Ambien, Lunesta, _nothing_ worked. You were exhausted and you wished you knew a way to put yourself to sleep (besides physically knocking yourself out. You had tried that, too, but you just woke up with a raging bruise an hour later).

So every night went the same. You took a hot shower, which was supposed to calm the nerves and make you sleepy. You followed all the Wiki How instructions to sleep to the best of your ability. Then you would typically lay in bed for around an hour, your eyes closed but you never quite reached that spot of pure, unimaginable, blank and unconscious bliss.

You hated it.

You hated it so, so very much. You didn’t have words to describe how much you hated your sleep insomnia, so instead of describing how much you hated it you would get onto your computer and spend your time fucking around on the internet until around 4 in the morning, to which, finally, you would fall asleep.

You sat there, around 3:30 in the morning, watching YouTube and painting your nails. Believe it or not, you had a fascination with colors and being an artist. With the last flick of your wrist, you painted your thumb a vibrant shade of sparkling, glittering blue. You admired your work before your gaze went back to your computer screen.

Every night, right around this time, your mom would wake up to use the bathroom. The sound of the toilet flushing overhead alerted to you that within an hour, you’d be asleep. Exhaustion and relief flooded through you. You wanted desperately to knock yourself out into a comfortable doze, and it seemed as if it was fast approaching.

You teased yourself for the next five minutes, knowing that forcing yourself to stay awake until absolute fatigue would result in you passing out. So you watched the rest of your video, letting your nails dry before shutting your laptop, putting it on the ground and curling up beneath your sheets for a well deserved night of sleep.

Or, just for a few hours before you had to go back to school.

It was slow, so slow, but then you were in that mindless blackness that you so craved.

Until the sound of your door opening hit your ears and you could have practically screamed if the rest of the house was asleep. The sound of footsteps coming into your room had you awake, now, and you could only assume it was your little brother.

You were going to kill him.

“Get the fuck out of my room, John, before I get the fuck up and strangle your stupid little ass for _actually fucking WAKING ME UP!”_ You turned on your light, your face red with rage and your heart beating erratically. Then you turned back to your brother only to _not_ find your brother.

“You’re… not John.” Before you stood a figure, bathed in black with a mask resembling the pigment of your painted nails. The thing stood like a human, but it was much, much more frightening than any old human. A black, tar-like substance dripped from the eye sockets of the blue mask, and you felt absolutely paralyzed.

 _This has to be sleep apnea. Please. Please please please oh my god please go away you scary thing please._ You thought to yourself, but you were able to move your eyes, wiggle your toes and turn on the lamp for fuck’s sake.

The thing only paused, tilting its head to the side as if curious.

“I can’t say that I am John.” It spoke in a deep, raspy voice. It approached you with long steps, and then it was at your bedside. You sat there, staring up at its eyes, or attempting to as there was literally nothing coming out.

Then you started screaming. It was the loudest thing you could think to do, and damn you did it well. You screamed and screamed until the thing’s gloved hand clamped around your mouth. The damage was done, though, and it hissed at you in annoyance and rage. You didn’t care, though. You finally were coming to your senses and you reached up to grab at the creature’s hand and wrist, lurching your body up from the bed to struggle.

Then your father was bursting into your basement bedroom. Your father was a _huge_ man with not an ounce of the word “small” on him. He was a mixture of fat and pure muscle, and nobody wanted to mess with him.

Especially this guy.

Your father was on the creature in an instant, prying it off of you with the strength of a wildebeest. The creature seemed almost as strong, though, but it’s agility and speed to get out of your father’s grasp. It landed on the floor on its legs before stepping back into the wall. The masked thing growled a low, angry growl resounding from the pit of its throat as it prepared to spring.

“Get the fuck out of my house before i-” Your father was interrupted as the thing launched itself at your father. But instead of attacking him, it sprung right over him before sprinting up the stairs. You remained on the bed, shock and anguish beginning to hit you full force.

This motherfucker not only threatened her but also disturbed her delicate sense of sleep.

 _How fucking dare son of a bitch. He better hope to never see me again. Wait, did I just refer to it as he? Oh, my god. It’s like I gave it a name. I’ll get attached, and then get Stockholm-_ You passed out.

 

Masky and Hoodie

_Rating: PG; suggestion of alcohol use._

You were nothing but a college student, missing your family, getting a majority of good grades and doing stupid shit on the days you didn’t have class. You were living the college dream, as most people liked to call it. You drank, smoked pot, fucked a little… You were having the time of your life.

You were also a hunter on the side. It wasn’t big or anything. All you did was research creeps around the world and report back to your “boss”. You were quick to pick up details from any recent murders even suspected of having an involvement with creepypastas. You were a hunter, and you had it as your main mission to kill as many of these motherfuckers as you could.

Or, at least, help kill them. You weren’t all that skilled with killing people. Blood made you nauseous.

After a good raging party at the frat house, you were on your way back to the dorm room. You were exhausted and drunk as hell. The dorm’s greeters eyed you up and down before letting you in, but not without saying a few choice words to “Don’t get caught lookin’ like that or you might get into some trouble with the police around here. You smell like whiskey.”

You roll your eyes at the front desk person. “I’m _fine.”_ You snark back before walking into the stairwell and made your way up. Tomorrow morning would be a doozy trying to do anything with the raging hangover that would soon arrive.

“Fuck me, I guess.” You mumble to yourself as you make it back to your dorm room. Your roommate was already fast asleep, and there was a body beside her. You raised a brow before realizing it was his boyfriend.

“Oh, ain’t that adorable.” You grin, taking out your phone to get some good candid shots to show your roommate in the morning. Then you face planted into your bed and passed out at around 2:33 AM.

You woke up at 11 from the sound of your alarm. Your head felt like it was going to split from the amount of pain you were under. At that point all you wanted to do was launch yourself from the roof to end the pain. Fuck you for drinking that much.

Your roommate and his boyfriend were still there. Rylin sat on the bed, an arm wrapped around your roommate, Trent. You looked at them through bleary eyes before remembering the photo you had taken of them.

“Guys… I came back last night and… you two were so fucking cute. I had to take a picture.” You said through the haze of your hangover. God, your head hurt. “Do you have any painkillers by the way?” You asked, yawning as you sat up to get your phone.

You were quick to unlock your phone. Trent shook his head at you.

“Y/n, you know you’re supposed to ask before taking pictures of us. Now show me the damn photo.” Rylin chuckled as you showed them your phone. Trent’s cheeks turned a rosy shade of red before burying his face into Rylin’s neck.

“That is so fucking awful yet so adorable. Why did you have to get me drooling, though?” Trent groaned as Rylin studied the picture.

“You have my number, right, Y/n? Send me that.” He said before his brows raised into his forehead.

“Um… check your text.” Rylin said, and you tilted your head to the side, confused. Your phone hadn’t buzzed or anything. You turned your phone to see a message from an unknown number. It disappeared before you had the chance to read it. “Yeah, I’ll send you it. Hold on, though.” You replied, crossing your legs on your bed as Trent handed you the bottle of painkillers.

“Thanks, man.” You said. You were quick to down four pills. Too bad you’d have to wait for the release. Then you were reading the message, and a surge of unease went through you.

_From: Unknown_

_Message: Hello, Y/n. We’ve heard quite a bit about you. We don’t like that you’re attempting to commit acts against our kind. Expect to see us soon._

You stared at the message in horror before you pulled up your computer to email your boss. _This is not good._


End file.
